Cesium carbonate → HCID 59013890, compound

HRID 907548Notes

Reaction equation

HRID 907548 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[OH:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[N:28]1[CH:33]=[CH:32][C:31]([CH2:34]Cl)=[CH:30][CH:29]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:34][C:31]2[CH:32]=[CH:33][N:28]=[CH:29][CH:30]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 11543684Tert-butyl 4-(2-hydroxyphenyl)piperazine-1-carboxylate

Product 1

HCID 59013890HCID 59013890, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2-Hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (18 mmol, 5 g), DMF (40 ml) and cesium carbonate (40 mmol, 13 g) was stirred at room temperature for 15 minutes, followed by addition of 4-picolyl chloride hydrochloride (18 mmol, 2.953 g). The resulting mixture was stirred at room temperature overnight. The reaction mixture was poured onto ice/water and extracted with ethyl acetate (3×). The combined organic layer was washed with Sat. NaCl. The crude product was purified on silica column using 75% EtOAc/hexanes to give 4-[2-(Pyridin-4-ylmethoxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (4.5 g).

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. additionThe reaction mixture was poured onto ice/water
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic layer was washed with Sat. NaCl
  5. customThe crude product was purified on silica column

Sources & evidence

ORD record
ord-d00c9a93f8e0429da7cacc56c8271957
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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